5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxylic acid | 1283629-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxylic acid
• 英文别名: 5-methyl-3-[1-[3-(trifluoromethyl)phenyl]indol-3-yl]-4H-1,2-oxazole-5-carboxylic acid
• CAS: 1283629-16-2
• 化学式: C₂₀H₁₅F₃N₂O₃
• 分子量: 388.346
• InChiKey: YLDWAFKIYBLEKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxylic acid 、 环己胺 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以33%的产率得到N-cyclohexyl-5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxamide
  参考文献：
  名称：

  Synthesis and biological activity of novel MIF antagonists

  摘要：

  Two series of novel furan and indole compounds were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds from both series inhibited the enzymatic activity of MIF at levels equal to or significantly better than ISO-1 (an early MIF inhibitor). The majority of the compounds that robustly inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells were from the furan series (compounds 5, 9, 13, 15, and 16). In contrast, compounds that markedly inhibited the MIF-induced production of pro-inflammatory cytokines were predominantly from the indole series (compounds 26, 29, and 32). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.127
• 作为产物：
  描述：

  1-(3-(trifluoromethyl)phenyl)-1H-indole-3-carbaldehyde 在 sodium hypochlorite 、 lithium hydroxide monohydrate 、 盐酸羟胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 水 为溶剂， 反应 35.0h， 生成 5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of novel MIF antagonists

  摘要：

  Two series of novel furan and indole compounds were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds from both series inhibited the enzymatic activity of MIF at levels equal to or significantly better than ISO-1 (an early MIF inhibitor). The majority of the compounds that robustly inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells were from the furan series (compounds 5, 9, 13, 15, and 16). In contrast, compounds that markedly inhibited the MIF-induced production of pro-inflammatory cytokines were predominantly from the indole series (compounds 26, 29, and 32). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.127